2D- and 3D- potential energy surfaces of β-(1→3)-linked disaccharides calculated with the MM3 force-field

The adiabatic conformational surfaces of sixteen 4′,6′,6-trideoxy-β-D-(1→3)-linked disaccharides were obtained using the MM3 force-field. Calculations were carried out on disaccharides with different configurations at C2, C4 and C2′, which are neighbors to the glycosidic linkage, as well as that of...

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Detalles Bibliográficos
Autores principales: Stortz, C.A., Cerezo, A.S.
Formato: JOUR
Materias:
Axial
Conformational analysis
Disaccharide maps
Equatorial
MM3
disaccharide
functional group
analytic method
article
calculation
computer program
conformational transition
correlation analysis
energy resource
entropy
linkage analysis
molecular mechanics
structure analysis
substitution reaction
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_07328303_v22_n3-4_p217_Stortz
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_07328303_v22_n3-4_p217_Stortz
record_format dspace
spelling todo:paper_07328303_v22_n3-4_p217_Stortz2023-10-03T15:37:33Z 2D- and 3D- potential energy surfaces of β-(1→3)-linked disaccharides calculated with the MM3 force-field Stortz, C.A. Cerezo, A.S. Axial Conformational analysis Disaccharide maps Equatorial MM3 disaccharide functional group analytic method article calculation computer program conformational transition correlation analysis energy resource entropy linkage analysis molecular mechanics structure analysis substitution reaction The adiabatic conformational surfaces of sixteen 4′,6′,6-trideoxy-β-D-(1→3)-linked disaccharides were obtained using the MM3 force-field. Calculations were carried out on disaccharides with different configurations at C2, C4 and C2′, which are neighbors to the glycosidic linkage, as well as that of the linked carbon (C3). The surfaces were plotted as contour maps and as 2D graphs representing the energy vs. the ψ angle. The resulting maps were similar in each case, indicating that the substituents do not play a major role in the conformational features of these disaccharides. However, the number of minima, the preferred minimum conformation and the flexibility depended on the configurations of the mentioned carbons. Vicinal equatorial substituents tend to decrease the overall flexibility, especially those on C2, although cross over effects were found. The relative stabilities of the minimal energy conformations of the 16 compounds were compared with those of their equivalent α-linked counterparts. Deviations of the predicted increased stabilities of equatorially substituted compounds over axially substituted ones follow a relationship with their configurations, and consequently can serve to formulate predictive trends. Fil:Stortz, C.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Cerezo, A.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_07328303_v22_n3-4_p217_Stortz
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Axial
Conformational analysis
Disaccharide maps
Equatorial
MM3
disaccharide
functional group
analytic method
article
calculation
computer program
conformational transition
correlation analysis
energy resource
entropy
linkage analysis
molecular mechanics
structure analysis
substitution reaction
spellingShingle Axial
Conformational analysis
Disaccharide maps
Equatorial
MM3
disaccharide
functional group
analytic method
article
calculation
computer program
conformational transition
correlation analysis
energy resource
entropy
linkage analysis
molecular mechanics
structure analysis
substitution reaction
Stortz, C.A.
Cerezo, A.S.
2D- and 3D- potential energy surfaces of β-(1→3)-linked disaccharides calculated with the MM3 force-field
topic_facet Axial
Conformational analysis
Disaccharide maps
Equatorial
MM3
disaccharide
functional group
analytic method
article
calculation
computer program
conformational transition
correlation analysis
energy resource
entropy
linkage analysis
molecular mechanics
structure analysis
substitution reaction
description The adiabatic conformational surfaces of sixteen 4′,6′,6-trideoxy-β-D-(1→3)-linked disaccharides were obtained using the MM3 force-field. Calculations were carried out on disaccharides with different configurations at C2, C4 and C2′, which are neighbors to the glycosidic linkage, as well as that of the linked carbon (C3). The surfaces were plotted as contour maps and as 2D graphs representing the energy vs. the ψ angle. The resulting maps were similar in each case, indicating that the substituents do not play a major role in the conformational features of these disaccharides. However, the number of minima, the preferred minimum conformation and the flexibility depended on the configurations of the mentioned carbons. Vicinal equatorial substituents tend to decrease the overall flexibility, especially those on C2, although cross over effects were found. The relative stabilities of the minimal energy conformations of the 16 compounds were compared with those of their equivalent α-linked counterparts. Deviations of the predicted increased stabilities of equatorially substituted compounds over axially substituted ones follow a relationship with their configurations, and consequently can serve to formulate predictive trends.
format JOUR
author Stortz, C.A.
Cerezo, A.S.
author_facet Stortz, C.A.
Cerezo, A.S.
author_sort Stortz, C.A.
title 2D- and 3D- potential energy surfaces of β-(1→3)-linked disaccharides calculated with the MM3 force-field
title_short 2D- and 3D- potential energy surfaces of β-(1→3)-linked disaccharides calculated with the MM3 force-field
title_full 2D- and 3D- potential energy surfaces of β-(1→3)-linked disaccharides calculated with the MM3 force-field
title_fullStr 2D- and 3D- potential energy surfaces of β-(1→3)-linked disaccharides calculated with the MM3 force-field
title_full_unstemmed 2D- and 3D- potential energy surfaces of β-(1→3)-linked disaccharides calculated with the MM3 force-field
title_sort 2d- and 3d- potential energy surfaces of β-(1→3)-linked disaccharides calculated with the mm3 force-field
url http://hdl.handle.net/20.500.12110/paper_07328303_v22_n3-4_p217_Stortz
work_keys_str_mv AT stortzca 2dand3dpotentialenergysurfacesofb13linkeddisaccharidescalculatedwiththemm3forcefield
AT cerezoas 2dand3dpotentialenergysurfacesofb13linkeddisaccharidescalculatedwiththemm3forcefield
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